DE548151C - Process for the production of combinations of polyvinyl esters and fatty oils - Google Patents
Process for the production of combinations of polyvinyl esters and fatty oilsInfo
- Publication number
- DE548151C DE548151C DEC44188D DEC0044188D DE548151C DE 548151 C DE548151 C DE 548151C DE C44188 D DEC44188 D DE C44188D DE C0044188 D DEC0044188 D DE C0044188D DE 548151 C DE548151 C DE 548151C
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- oils
- fatty oils
- polyvinyl esters
- combinations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- 229920001290 polyvinyl ester Polymers 0.000 title claims description 11
- 239000010685 fatty oil Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003921 oil Substances 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 229920001567 vinyl ester resin Polymers 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
- 229960003328 benzoyl peroxide Drugs 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 235000021388 linseed oil Nutrition 0.000 description 5
- 239000000944 linseed oil Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000001293 FEMA 3089 Substances 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013066 combination product Substances 0.000 description 1
- 229940127555 combination product Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof
- D06M15/333—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof of vinyl acetate; Polyvinylalcohol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Verfahren zur Herstellung von Kombinationen aus Polyvinylestern und fetten Ölen Man hat sich bisher vergeblich bemüht, Polyvinylester mit fetten Ölen zu beständigen, homogenen Verbindungen zu vereinigen. Ein Verfahren, das diese Kombination gestattet, würde die Anwendungsmöglichkeiten der Polyvinylester ganz außerordentlich erweitern und würde neben anderen Verwendungsgebieten den Polyvinylestern auch die Verwendung im Öllackgebiet eröffnen.Process for the preparation of combinations of polyvinyl esters and fatty oils One has tried in vain to use polyvinyl esters with fatty oils to unite into stable, homogeneous connections. A process that this combination allowed, the application possibilities of the polyvinyl esters would be quite extraordinary expand and, in addition to other areas of use, would also include the polyvinyl esters Open use in the oil varnish area.
Es ist nun gelungen, die Kombination der Ptilyvinylester mit fetten Ölen zu verwirklichen. Es gelingt dies überraschenderweise dann, wenn man die Polymerisation der Vinylester in Gegenwart von niedrigdispersen Phasen fetter Öle sich vollziehen läßt. Es bleibt hierbei dahingestellt, ob sich ztt gleicher Zeit auch eine Polvmerisation der fetten Öle in irgendeiner Weise abspielt. Der Polymerisationsvorgang selbst kann auf irgendeine Weise ausgelöst werden, z. B. durch Katalysatoren, durch Druck, durch Belichtung u. dgl., selbstverständlich auch .durch Kombination der einzelnen Polymerisationsmaßnahmen oder nach anderen bekannt gewordenen Arbeitsverfahren, z. B. nach Patent 4.90 o4.r. Das Mengenverhältnis zwischen den Vinylestern und diesen Ölphasen läßt sich innerhalb weiter Grenzen variieren. Zur Durchführung des Verfahrens mischt man einen Vinylester oder ein Vinylestergemisch in dem gewünschten Verhältnis mit einer oder mehreren niedrigdispersen Phasen von fetten Ölen oder einem Gemisch derselben und bringt dieses Reaktionsgemisch zur Polymerisation. Man kann auch so verfahren, daß man durch Anwendung geeigneter Zusatzstoffe, wie Harze, Weichmachungsmittel. Lösungsmittel u. dgl., den Reaktionsverlauf bzw. die Natur der entstehenden Polymerisationsprodukte nach Belieben beeinflußt. Eine anäerweitige willkürliche Beeinflussung der Reaktionsprodukte kann durch zeitgemäßes Unterbrechen des Polymerisationsvorganges geschehen. Man kann unter Umständen auch so verfahren, daß man zu einem bereits in Polymerisation befindlichen Vinylester bzw. Vinylestergemisch die Phase oder ein Phasengemisch hinzufügt oder umgekehrt im Schoße einer Phase oder eines Phasengemisches arbeitet.It has now been possible to combine the Ptilyvinylester with fatty Realize oils. Surprisingly, this succeeds if the polymerization the vinyl ester take place in the presence of low-dispersion phases of fatty oils leaves. It remains to be seen whether there will also be a polymerisation at the same time of fatty oils in some way. The polymerization process itself can be triggered in any way, e.g. B. by catalysts, by pressure, by exposure and the like, of course also by combining the individual Polymerization measures or other known work processes, z. B. according to patent 4.90 o4.r. The quantitative ratio between the vinyl esters and these Oil phases can be varied within wide limits. To carry out the procedure a vinyl ester or a vinyl ester mixture is mixed in the desired ratio with one or more low-dispersion phases of fatty oils or a mixture the same and causes this reaction mixture to polymerize. You can do that too process that one by using suitable additives, such as resins, plasticizers. Solvents and the like, the course of the reaction or the nature of the polymerization products formed influenced at will. An additional, arbitrary influence on the reaction products can be done by interrupting the polymerization process in a timely manner. Man can possibly also proceed in such a way that one is already in polymerization vinyl ester or vinyl ester mixture present the phase or a phase mixture adds or, conversely, works in the bosom of a phase or a mixture of phases.
Als Beispiel der für dieses Verfahren geeigneten fetten Öle seien die durch das Patent 546 679 bekannt gewordenen niedrigdispersen Phasen genannt, z. B. die niedrigdispersen Phasen der Lein-, Soja-, Perilla-, Holz-, Mohn- u. dgl. Standöle, und auch solche niedrigdisperse Phasen enthaltende Öle.An example of the fatty oils suitable for this process are the low-dispersion phases made known by patent 546 679, z. B. the low-dispersed phases of flax, soy, perilla, wood, poppy seeds and the like. Stand oils, and also oils containing such low-dispersion phases.
Durch das vorstehende Verfahren erhält man Produkte, deren Eigenschaften Resultanten aus den Eigenschaften der Komponenten sind. Es gelingt, Ölpolyvinylesterverbindungen herzustellen, in denen das Verhältnis der Komponenten im weitesten Maße variiert werden kann, wobei beispielsweise Kombinationen erhalten werden, die aus 95 °%o 0I und 5 % Polyvrinylester bestehen. Infolgedessen besteht eine sehr große Mannigfaltigkeit in -der Herstellung, Konstitution und Verwendung.. Man kann.-auf -diese _Waise unter anderem Produkte herstellen,- die. in üblichen organischen Lösungsmitteln, besonders auch in Terpentinöl, in Sangajol, Tetrahydronaphthalin o. dgl., löslich sind. Diese Produkte sind geeignet für die Lackindustrie, besonders zur Herstellung von Öllacken, Ölkombinationslacken, für Rostschutzanstriche u. dgl., selbstverständlich auch in Kombination mit Pigmenten, Füllstoffen. anderen Lackstoffen, Ölen, Sikkativen usw., ferner in der Klebstoffindustrie, besonders für die Herstellung irreversibler Klebstoffe u. dgl. Die unlöslichen bzw. schwer-löslichen Formen sind u. a. zur Zierstellung von Preßmaterialien aller Art usw. geeignet.The above process gives products, their properties Are resultants from the properties of the components. It succeeds in oil polyvinyl ester compounds produce in which the ratio of the components varies widely can be obtained, for example combinations are obtained that consist of 95% o 0I and 5% polyvinyl ester. As a result, there is great diversity in -the manufacture, constitution and use .. One can -this _Waise, among other things, produce products - the. in common organic solvents, especially soluble in turpentine oil, sangajol, tetrahydronaphthalene or the like are. These products are suitable for the paint industry, especially for manufacturing of oil varnishes, oil combination varnishes, for anti-rust coatings and the like, of course also in combination with pigments, fillers. other paints, oils, siccatives etc., also in the adhesives industry, especially for the manufacture of irreversible Adhesives and the like. The insoluble or sparingly soluble forms include the following. for decorative position of all kinds of pressing materials, etc. suitable.
Die nachfolgenden Beispiele sollen das Verfahren charakterisieren, wobei aber betont wird, daß der aufgefundene Weg eine außerordentlich große Mannigfaltigkeit hinsichtlich der Herstellungsmethoden und der Produkte offenläßt.The following examples are intended to characterize the process but it is emphasized that the path that has been found is extraordinarily diverse leaves open with regard to the production methods and the products.
Beispiel i Zoo kg v inylacetat werden mit 5o kg niedrigdisperser Leinstandölphase unter Rühren gemischt und mit 16oo g Benzoylsuperoxyd durch Erwärmen zur Reaktion gebracht. Nachdem die Masse eine dickflüssige Konsistenz angenommen hat, wird die Polymerisation durch rasches Abkühlen unterbrochen. Das nach Abdestillation des unverbrauchten Vinylacetats erhaltene zähe Produkt ist auch in Terpentinöl, Sangajol und Tetrahydronaphthalin klar löslich und für Lacke aller Art, Spachtelmassen u. dgl. geeignet.Example 1 kg of vinyl acetate are mixed with 50 kg of low-dispersion linseed oil phase mixed with stirring and reacted with 160 g of benzoyl peroxide by heating brought. After the mass has taken on a thick consistency, the Polymerization interrupted by rapid cooling. After distilling off the The tough product obtained from unconsumed vinyl acetate is also found in turpentine oil, sangajol and tetrahydronaphthalene clearly soluble and for paints of all kinds, fillers and the like. Like. Suitable.
Beispiel e Setzt man die in Beispiel i beschriebene Polymerisation weiter fort; so erhält man schließlich ein festes, elastisches Produkt, das die in Beispiel i hervorgehobene Löslichkeit in Terpentinöl, Sangajol und Tetrahydronaphthalin nicht mehr besitzt, aber auch bei niedrigen Temperaturen elastisch bleibt.Example e If the polymerization described in Example i is used further on; so one finally obtains a firm, elastic product, which the in example i highlighted solubility in oil of turpentine, sangajol and tetrahydronaphthalene no longer possesses, but remains elastic even at low temperatures.
Beispiel 3 Eine Mischung aus 9o kg Vinylacetat und ro kg Vinylbutyrat wird mit 2o kg niedrigdisperser Sojastandölphase gemischt und nach Zusatz von i5oo g Benzoylsupero-xyd durch Erwärmen zur Polymerisation gebracht und im übrigen wie nach - Beispiel i behandelt. Auch dieses Produkt ist in üblichen Lacklösungsmitteln löslich.Example 3 A mixture of 90 kg vinyl acetate and ro kg vinyl butyrate is mixed with 20 kg of low-dispersion soya oil phase and after adding 1500 g benzoyl superoxide brought to polymerization by heating and otherwise as treated according to - example i. This product is also in common paint solvents soluble.
Beispiel q.Example q.
2 kg Vinylbutyrat werden mit 2 kg niedrigdisperser Leinstandölphase gemischt, mit 2o g Benzoylsuperoxyd versetzt, worauf durch Erwärmen die Polymerisation eingeleitet wird. Ist das Reaktionsgemisch dickflüssig geworden, wird die Reaktion unterbrochen. Nach Abdestillation von unverbrauchtem Vinylester wird ein in Sangajol klar lösliches Produkt erhalten.2 kg of vinyl butyrate are mixed with 2 kg of low-dispersion linseed oil phase mixed, mixed with 20 g of benzoyl peroxide, whereupon the polymerization by heating is initiated. If the reaction mixture has become thick, the reaction will interrupted. After unused vinyl ester has been distilled off, an in Sangajol Clearly soluble product obtained.
Beispiel 5 25 kg Leinstandöl von der Jodzahl ioi werden in 325 kg Vinylacetat gelöst. Die Lösung wird mit 32,5 g Benzoylsuperoxyd versetzt und dann 12 Stunden lang am Rückflußkühler gekocht. Daran anschließend wird der größte Teil des nicht polymerisierten Vinylacetats abdestilliert. Der Rest des Vinylacetats wird durch überhitzten Butanoldampf abgetrieben. Die gebildete Verbindung von Polyvinylacetat mit Öl wird durch Auswaschen mit u-Butylalkohol von den aus dem Leinstandöi stammenden Verunreinigungen (gesättigte Glyceride, freie Fettsäuren usw.) befreit.Example 5 25 kg of linseed oil with an iodine number are dissolved in 325 kg of vinyl acetate. The solution is mixed with 32.5 g of benzoyl peroxide and then refluxed for 12 hours. Most of the unpolymerized vinyl acetate is then distilled off. The remainder of the vinyl acetate is driven off by superheated butanol vapor. The resulting compound of polyvinyl acetate with oil is freed from the impurities (saturated glycerides, free fatty acids, etc.) originating from the linseed oil by washing with u-butyl alcohol.
Beispiel 6 2 kg Vinylbutyrat werden mit 2 kg eines Leinstandöles von der Jodzahl 148 gemischt, mit ioo g Benzoylsuperoxyd versetzt, worauf durch Erwärmen die Polymerisation eingeleitet wird. Sind 8o % des Vinylesters polymerisiert, wird die Reaktion unterbrochen. Nach Abdestillation von unverbrauchtem Vinylester wird das Produkt wie nach Beispiel 5 weiterbehandelt.EXAMPLE 6 2 kg of vinyl butyrate are mixed with 2 kg of linseed stand oil with an iodine number of 148, 100 g of benzoyl peroxide are added, whereupon the polymerization is initiated by heating. When 80% of the vinyl ester has polymerized, the reaction is interrupted. After unused vinyl ester has been distilled off, the product is treated further as in Example 5.
In dem Patent 281687, das die Herstellung von Polyvinylestern behandelt, wird darauf hingewiesen, daß die Eigenschaften der Polyvinylester durch Zusätze der verschiedensten Natur modifiziert werden können. Es wird dort keine chemische Wirkung der Ölzusätze festgestellt. Vielmehr ist das Ergebnis all dieser Zusätze verschiedener Natur nichts als ein Mischungsprodukt hinsichtlich der Farbe, der Durchsichtigkeit, der Härte und Biegsamkeit. Die wesentlichen Eigenschaften der Polyvinylester selbst und der Öle bleiben dabei unverändert.In patent 281687, which deals with the manufacture of polyvinyl esters, it should be noted that the properties of the polyvinyl ester by additives of the most varied nature can be modified. There won't be any chemical there Effect of the oil additives noted. Rather, it is the result of all of these additions of different nature, nothing but a mixture product with regard to the color that Transparency, hardness and flexibility. The main characteristics of the Polyvinyl ester itself and the oils remain unchanged.
Beispiel Ein Gemisch von 5 kg Lackleinöl, ,45 kg Vinylacetat und o,675 kg Benzoylsuperoxyd wird so lange gekocht, wie entnommene Proben noch eine Zunahme der Polymerisation anzeigen. Nach dem Abtreiben von unverbrauchtem Vinylacetat wird ähnlich wie bei Beispiel 5 aus dem gebildeten Kombinationsprodukt mit Isopropylalkohol der hochdisperse Anteil extrahiert.EXAMPLE A mixture of 5 kg of linseed oil, .45 kg of vinyl acetate and 0.675 kg of benzoyl peroxide is boiled for as long as the samples taken still indicate an increase in the polymerization. After unused vinyl acetate has been stripped off, the highly disperse fraction is extracted from the combination product formed with isopropyl alcohol in a manner similar to that in Example 5.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC44188D DE548151C (en) | 1929-12-31 | 1930-01-01 | Process for the production of combinations of polyvinyl esters and fatty oils |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE367102X | 1929-12-31 | ||
| DEC44188D DE548151C (en) | 1929-12-31 | 1930-01-01 | Process for the production of combinations of polyvinyl esters and fatty oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE548151C true DE548151C (en) | 1932-04-11 |
Family
ID=25851185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC44188D Expired DE548151C (en) | 1929-12-31 | 1930-01-01 | Process for the production of combinations of polyvinyl esters and fatty oils |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE548151C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE763840C (en) * | 1937-05-10 | 1955-02-14 | Chemische Forschungs Gmbh | Process for the preparation of polymeric vinyl alcohols |
-
1930
- 1930-01-01 DE DEC44188D patent/DE548151C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE763840C (en) * | 1937-05-10 | 1955-02-14 | Chemische Forschungs Gmbh | Process for the preparation of polymeric vinyl alcohols |
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